CA1134857A - Process for the preparation of terephthalic acid by the hydrolysis of intermediate stage crude dimethyl terephthalate - Google Patents
Process for the preparation of terephthalic acid by the hydrolysis of intermediate stage crude dimethyl terephthalateInfo
- Publication number
- CA1134857A CA1134857A CA000342255A CA342255A CA1134857A CA 1134857 A CA1134857 A CA 1134857A CA 000342255 A CA000342255 A CA 000342255A CA 342255 A CA342255 A CA 342255A CA 1134857 A CA1134857 A CA 1134857A
- Authority
- CA
- Canada
- Prior art keywords
- terephthalic acid
- hydrolysis
- crude
- water
- reactor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 336
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title claims abstract description 196
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 103
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 103
- 238000000034 method Methods 0.000 title claims abstract description 88
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 138
- 229910001868 water Inorganic materials 0.000 claims abstract description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 84
- 239000006227 byproduct Substances 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 51
- 239000000047 product Substances 0.000 claims abstract description 44
- 239000007791 liquid phase Substances 0.000 claims abstract description 31
- 230000003647 oxidation Effects 0.000 claims abstract description 30
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 30
- 239000011541 reaction mixture Substances 0.000 claims abstract description 30
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000004821 distillation Methods 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 238000009835 boiling Methods 0.000 claims abstract description 13
- 230000032050 esterification Effects 0.000 claims abstract description 10
- 238000005886 esterification reaction Methods 0.000 claims abstract description 10
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000007789 gas Substances 0.000 claims abstract description 5
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 239000012452 mother liquor Substances 0.000 claims description 43
- 239000000725 suspension Substances 0.000 claims description 41
- 239000007787 solid Substances 0.000 claims description 27
- 239000013078 crystal Substances 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 23
- 239000008346 aqueous phase Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 7
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 abstract description 14
- 229920000728 polyester Polymers 0.000 abstract description 12
- 239000000835 fiber Substances 0.000 abstract description 10
- 238000001953 recrystallisation Methods 0.000 abstract description 8
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 49
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 42
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 36
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 23
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000005406 washing Methods 0.000 description 14
- 239000012535 impurity Substances 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 238000011084 recovery Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl terephthalate Chemical compound 0.000 description 6
- 239000010802 sludge Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 230000000630 rising effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 2
- WMZNGTSLFSJHMZ-UHFFFAOYSA-N 3-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=CC(C(O)=O)=C1 WMZNGTSLFSJHMZ-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005275 alloying Methods 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009884 interesterification Methods 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2916197A DE2916197C2 (de) | 1979-04-21 | 1979-04-21 | Verfahren zur Herstellung von Terephthalsäure aus Dimethyltherephthalat als Zwischenprodukt |
| DEP2916197.5 | 1979-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1134857A true CA1134857A (en) | 1982-11-02 |
Family
ID=6068923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000342255A Expired CA1134857A (en) | 1979-04-21 | 1979-12-19 | Process for the preparation of terephthalic acid by the hydrolysis of intermediate stage crude dimethyl terephthalate |
Country Status (28)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3011858C2 (de) * | 1979-04-21 | 1982-11-25 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Terephtalsäure aus Roh-Dimethylterephthalat durch kontinuierliche Hydrolyse mit Wasser |
| DE3041293A1 (de) * | 1979-04-21 | 1982-06-16 | Dynamit Nobel Ag, 5210 Troisdorf | Verbessertes verfahren zur herstellung von terephthalsaeure aus dimethylterephthalat als zwischenprodukt |
| DE2938163A1 (de) * | 1979-09-21 | 1981-04-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von terephthalsaeure aus dimethylterephthalat als zwischenprodukt |
| DE3044617C2 (de) * | 1980-11-27 | 1985-09-26 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Terephthalsäure aus Dimethylterephthalat als Zwischenprodukt |
| JPS5983309A (ja) * | 1982-11-05 | 1984-05-14 | 三菱電機株式会社 | ガス遮断器 |
| DE3407912C1 (de) * | 1984-03-03 | 1985-05-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Terephthalsaeure ueber Terephthalsaeuredimethylester aus p-Xylol und Methanol |
| DE3904586A1 (de) * | 1989-02-16 | 1990-08-23 | Huels Chemische Werke Ag | Verfahren zur herstellung von dmt-zwischenprodukt bestimmter reinheit sowie dessen weiterverarbeitung zu reinst-dmt und/oder mittel- oder hochreiner terephthalsaeure |
| US5563294A (en) * | 1991-12-19 | 1996-10-08 | Amoco Corporation | Process for preparing purified 2,6-naphthalenedicarboxylic acid |
| ES2093404T5 (es) * | 1991-12-19 | 2001-11-16 | Bp Corp North America Inc | Proceso para preparar acido 2,6-naftalenodicarboxilico purificado. |
| US5886057A (en) * | 1993-07-05 | 1999-03-23 | E. I. Du Pont De Nemours And Company | Production of dicarboxylic acids |
| EP0725054A1 (de) * | 1995-01-24 | 1996-08-07 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von Terephthalsäure und ihrer Isomeren |
| US6472557B1 (en) | 1999-02-10 | 2002-10-29 | Eastman Chemical Company | Process for recycling polyesters |
| JP2006143612A (ja) * | 2004-11-17 | 2006-06-08 | Teijin Ltd | スラリーの送液方法 |
| CN101535370A (zh) | 2006-11-07 | 2009-09-16 | 帝人纤维株式会社 | 对苯二甲酸-烷撑二醇混合物的制备方法 |
| KR20120027531A (ko) | 2009-06-16 | 2012-03-21 | 아미리스 인코퍼레이티드 | 시클로헥센 1,4-카르복실레이트 |
| WO2010148080A2 (en) | 2009-06-16 | 2010-12-23 | Draths Corporation | Cyclohexane 1,4 carboxylates |
| US8415496B2 (en) | 2009-06-16 | 2013-04-09 | Amyris, Inc. | Biobased polyesters |
| WO2010148063A2 (en) | 2009-06-16 | 2010-12-23 | Draths Corporation | Cyclohexene 1,4-carboxylates |
| US8426639B2 (en) | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| PL3844140T3 (pl) * | 2018-08-30 | 2023-08-21 | NextChem S.p.A. | Sposób i aparatura do wytwarzania kwasów tłuszczowych z estrów metylowych w procesie niekatalitycznym |
| US10752776B2 (en) | 2018-09-19 | 2020-08-25 | International Business Machines Corporation | Cyclic bio-renewable flame retardants |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1112973B (de) * | 1954-09-08 | 1961-08-24 | Ici Ltd | Vorrichtung zur Reinigung von Terephthalsaeure |
| US2794832A (en) * | 1955-06-20 | 1957-06-04 | Shell Dev | Crystallization and separation of crystals |
| US2992168A (en) * | 1959-07-09 | 1961-07-11 | Eastman Kodak Co | Process of purifying dimethyl terephthalate and other compounds which sublime |
| US3108132A (en) * | 1962-01-16 | 1963-10-22 | Standard Oil Co | Purification of dmt by filtration |
| US3396087A (en) * | 1966-01-10 | 1968-08-06 | Exxon Research Engineering Co | Dimethylterephthalate recovery from paraxylene feed |
| GB1130695A (en) * | 1966-04-18 | 1968-10-16 | Hercules Inc | Production of terephthalic acid by hydrolysis of an alkyl terephthalate |
| DE1299627B (de) | 1966-08-31 | 1969-07-24 | Dynamit Nobel Ag | Verfahren zur Herstellung von reinster Terepthalsaeure |
| DE2010137C3 (de) | 1970-03-04 | 1979-07-05 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Terephthalsauredimethylester |
| US4118313A (en) * | 1973-11-03 | 1978-10-03 | Dynamit Nobel Aktiengesellschaft | Process and apparatus for mass transfer between heterogeneous systems |
-
1979
- 1979-04-21 DE DE2916197A patent/DE2916197C2/de not_active Expired
- 1979-06-21 DK DK259979A patent/DK259979A/da unknown
- 1979-07-02 YU YU1596/79A patent/YU42487B/xx unknown
- 1979-07-05 IT IT49662/79A patent/IT1162607B/it active
- 1979-07-06 NL NLAANVRAGE7905318,A patent/NL188036C/xx not_active IP Right Cessation
- 1979-07-10 MX MX178417A patent/MX153587A/es unknown
- 1979-07-13 JP JP8832279A patent/JPS55141433A/ja active Granted
- 1979-07-16 CS CS794967A patent/CS216849B2/cs unknown
- 1979-07-18 ZA ZA00793646A patent/ZA793646B/xx unknown
- 1979-07-19 ES ES482621A patent/ES482621A1/es not_active Expired
- 1979-07-20 FR FR7918841A patent/FR2454432B1/fr not_active Expired
- 1979-07-25 BR BR7904770A patent/BR7904770A/pt not_active IP Right Cessation
- 1979-07-26 AR AR277475A patent/AR217177A1/es active
- 1979-08-13 PL PL1979217729A patent/PL123543B1/pl unknown
- 1979-08-17 PT PT70080A patent/PT70080A/pt unknown
- 1979-08-20 RO RO7998485A patent/RO80178A/ro unknown
- 1979-09-03 BE BE0/196991A patent/BE878566A/xx not_active IP Right Cessation
- 1979-09-27 US US06/079,253 patent/US4302595A/en not_active Expired - Lifetime
- 1979-11-20 DD DD79217017A patent/DD146822A5/de not_active IP Right Cessation
- 1979-11-26 PH PH23328A patent/PH22194A/en unknown
- 1979-12-19 CA CA000342255A patent/CA1134857A/en not_active Expired
-
1980
- 1980-01-12 EG EG22/80A patent/EG14817A/xx active
- 1980-04-02 IN IN382/CAL/80A patent/IN154606B/en unknown
- 1980-04-15 TR TR21461A patent/TR21461A/xx unknown
- 1980-04-18 GB GB8012888A patent/GB2047704B/en not_active Expired
- 1980-04-18 BG BG047456A patent/BG60054B2/bg unknown
- 1980-04-18 SU SU802910350A patent/SU1041029A3/ru active
- 1980-04-18 UA UA2910350A patent/UA7015A1/uk unknown
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